Secrets, Personal Data, and Other People's Work

Now that Tessa knows where her words travel, she can draw the line every workplace needs: what never goes into the chat box at all. Not "what is risky", not "what makes me uneasy" — a short list of categories that stay out regardless of how convenient the task is and how good the provider's policy looks.

There are three of them: credentials, personal data about real people, and confidential material that is not hers to share. They are on the list for the same reason. For these, "probably handled fine" is not a standard. The previous page's answers are promises about the ordinary case, and these are the items where the unusual case is the one that ends up with somebody's name attached to it.

Credentials: No Exceptions

A credential is anything that unlocks something: a password, a door code, an access token, the recovery answer to a security question, the number on a company card. If knowing it lets someone in, it is a credential.

These never go in the box, and this is the one rule on the page with no shading. The reason is not that the provider is untrustworthy. It is that a pasted secret lands in a chat history and in service logs, in a system Tessa does not administer, under a retention policy she does not set — and a secret that has travelled is no longer a secret in any useful sense. She cannot inspect where the copies are, and she cannot delete them. The only real repair is to change the secret itself, which usually means an awkward conversation with whoever owns it.

The rule sounds obvious right up until the moment it is inconvenient — a script that will not run, an error message that happens to include a key, a colleague asking for help with a login problem. That is exactly the moment it is protecting. And it is worth building now, because in Chapter 7 Tessa gets a credential of her own: a key that identifies her to the provider and spends real money on her behalf. By then this rule will already be muscle memory, which is the only reliable way to have it.

Personal Data: Other People's, Especially

Personal data is anything that identifies a real person or attaches facts to an identified one: a name plus a booking reference, a passport number, a home address, a payment detail, a note about someone's health or their difficult divorce. Waymark's files are full of it, because a travel agency runs on it.

The point is who gave it to whom. A guest handed those details to Waymark — to book a trip, in a specific relationship, with expectations attached. They did not hand them to Waymark's chat provider, and Tessa is not the person entitled to forward them onward.

Here is the test that settles most cases in three seconds. Waymark sometimes hires an outside contractor: capable, professional, not an employee, and someone the guest has never heard of. Would you email this material to that contractor, unprompted, without asking anyone first? A draft brochure, gladly. The client list, obviously not. The chat provider sits in exactly the contractor's position — an outside company doing work for you — so the same instinct applies, and it is an instinct most people already have.

And then the part that turns this from a prohibition into a technique: strip the identifying details and paste the rest. "A guest" instead of Mrs Ellison. "A booking three days before departure" instead of the reference number. The model was never helping because it knew who the guest was; it was helping because it could see the situation, the tone, and the shape of the problem. All of that survives the swap intact.

Confidential Material: Not Yours to Move

The third category is material that belongs to someone else's confidence: the unsigned supplier contract, a colleague's unpublished plan, the pricing a partner shared while a deal is being negotiated, anything covered by an NDA — a signed promise to keep a document inside a defined circle of people.

Confidentiality is not really about secrecy in the dramatic sense. It is about relocation: you undertook not to move this material outside a circle, and the provider is outside the circle. That follows directly from the previous page — the provider is a separate company, receiving, processing and storing what you send. Pasting the unsigned supplier contract into a chat box is moving it, whatever the intention was.

Ownership is the whole test, and it cuts both ways. Tessa's own draft brochure is hers to paste. The same brochure, a week before a partner announcement, under an agreement she signed, is not — and nothing about the text changes in between. Ask whose material it is and who was promised what, not how sensitive it feels.

The Redaction Habit

Redaction is removing or replacing the identifying details before sharing something. It is unglamorous, it takes about two minutes, and it converts most "I can't use AI for this" tasks into "here is how I use AI for this".

The method is one question: what does the model actually need to see in order to help? For a difficult complaint letter, it needs the sequence of events, the tone of the guest, and what Waymark is offering. It does not need the guest's name, the card digits, the booking reference, or the phone number. Replace names with roles, dates with relative timing where the exact date does not matter, and account numbers with nothing at all. Keep the structure; drop the identity.

What comes back is a draft with placeholders where the private details were, and Tessa puts the real ones back herself in ten seconds. The answer is not worse for having been asked about "a guest". That is what makes redaction worth learning as a habit rather than an inconvenience: it is protection that enables work instead of forbidding it.

One last argument for making these three categories a bright line rather than a case-by-case judgement call. Judgement is excellent at eleven in the morning. At ten to five, with a deadline and a full inbox, judgement quietly starts agreeing with whatever is fastest. A list does not get tired, which is precisely why it is written down as a list.